WO2019017386A1 - Composé, substrat de formation de motif, agent de couplage et procédé de formation de motif - Google Patents

Composé, substrat de formation de motif, agent de couplage et procédé de formation de motif Download PDF

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Publication number
WO2019017386A1
WO2019017386A1 PCT/JP2018/026909 JP2018026909W WO2019017386A1 WO 2019017386 A1 WO2019017386 A1 WO 2019017386A1 JP 2018026909 W JP2018026909 W JP 2018026909W WO 2019017386 A1 WO2019017386 A1 WO 2019017386A1
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Prior art keywords
group
compound
substrate
pattern
general formula
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PCT/JP2018/026909
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English (en)
Japanese (ja)
Inventor
雄介 川上
山口　和夫
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株式会社ニコン
学校法人神奈川大学
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Priority to CN201880046689.8A priority Critical patent/CN110891955A/zh
Publication of WO2019017386A1 publication Critical patent/WO2019017386A1/fr
Priority to US16/744,949 priority patent/US11767327B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/621—Providing a shape to conductive layers, e.g. patterning or selective deposition
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to a compound, a substrate for pattern formation, a coupling agent, and a method for pattern formation.
  • Patent Document 1 describes a fluorine-containing compound whose contact angle can be changed before and after light irradiation.
  • Patent No. 4997765 gazette
  • a first aspect of the present invention is a compound represented by the following general formula (1).
  • X 01 is a group showing a semiconductor characteristic.
  • Y is a divalent linking group.
  • a second aspect of the present invention is a patterning substrate having a surface chemically modified with the compound of the first aspect of the present invention.
  • a third aspect of the present invention is a coupling agent comprising the compound of the first aspect of the present invention.
  • a fourth aspect of the present invention is a pattern forming method for forming a pattern on the surface to be treated of an object, wherein at least a part of the surface to be treated of the object is aminated to form an aminated surface. And a second step of chemically modifying the aminated surface using the compound of the first aspect of the present invention.
  • a fifth aspect of the present invention is a method of forming a pattern on a surface to be treated of an object, wherein the treatment is carried out using a first photodegradable coupling agent containing a compound having a photoresponsive group. After the step A of aminating at least a part of the surface, and the step A, using the first coupling agent containing a compound containing a group having a semiconductor characteristic, the group having a semiconductor characteristic is treated on the surface to be treated
  • a pattern forming method comprising the step of introducing B, and the step C of introducing a group having semiconductor characteristics using the second coupling agent containing the compound according to claim 1 or 2 after the step B. is there.
  • a sixth aspect of the present invention is a compound represented by the following general formula (B1).
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R 12 represents a thiophene skeleton Is a substituent having L is a divalent linking group containing (-NH-) and a methylene group.
  • a seventh aspect of the present invention is a compound represented by the following general formula (B1) -1.
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R 12 represents It is a substituent having a thiophene skeleton.
  • n represents an integer of 0 or more.
  • the present embodiment is a compound represented by the following general formula (1).
  • the compound of the present embodiment includes an active carbonate structure and a group having semiconductor characteristics. For this reason, the compound of the present embodiment can simultaneously carry out the modification of the aminated substrate and the introduction of the semiconductor characteristic group. That is, by using the compound of the present invention, for example, the step of forming the wiring-forming base film can be omitted, and the organic semiconductor base film can be formed.
  • X 01 is a group showing a semiconductor characteristic.
  • Y is a divalent linking group.
  • X 01 is a group showing semiconductor characteristics.
  • semiconductor characteristics refer to the change in conductivity due to external stimuli such as light and voltage, and in particular means the characteristics in which the drain-source current changes with gate voltage.
  • the group exhibiting semiconductor characteristics as X 01 is preferably a group obtained by removing one hydrogen atom from a compound exhibiting semiconductor characteristics.
  • the following compounds are mentioned as a compound which shows semiconductor characteristics.
  • Thiophenes such as pentacene, rubrene, tetracene and other acenes, benzodithiophene (BDT), benzothienobenzothiophene (BTBT), dinaphthothienothiophene (DNTT), dinaphthobenzodithiophene (DNBDT) as a p-type semiconductor is there.
  • n-type semiconductors include perylenes such as perylene diimide (PTCDI), quinones such as tetracyanoquinodimethane (TCNQ), and fullerenes such as C60.
  • PTCDI perylene diimide
  • TCNQ quinones
  • TCNQ tetracyanoquinodimethane
  • fullerenes such as C60.
  • a compound having a soluble structure such as an alkyl group or an alkylsilyl group may be used as the compound having such semiconductor characteristics.
  • Such compounds include, for example, soluble pentacenes such as TIPS pentacene (6, 13-bis (triisopropylsilylethynyl) pentacene).
  • Y is a divalent linking group.
  • Y is not particularly limited, but preferable examples thereof include a divalent hydrocarbon group which may have a substituent, a divalent linking group containing a hetero atom, and the like.
  • the hydrocarbon group which may have a substituent is preferably an aliphatic hydrocarbon group.
  • the aliphatic hydrocarbon group include linear or branched aliphatic hydrocarbon groups, and aliphatic hydrocarbon groups having a ring in the structure.
  • a linear or branched aliphatic hydrocarbon group is preferable, and a linear or branched alkylene group having 1 to 20 carbon atoms is preferable, and a linear chain of 1 to 15 carbon atoms is preferable.
  • a branched alkylene group is more preferable, and a linear or branched alkylene group of 1 to 10 is further preferable.
  • the general formula (1) is preferably the following general formula (1) -1.
  • Y 01 is an alkylene group having 1 to 20 carbon atoms
  • X 01 is a group exhibiting semiconductor characteristics.
  • Y 01 includes the same groups as the alkylene groups exemplified for Y, and among them, a linear alkylene group is preferable, and an alkylene group having 4 to 15 carbon atoms is preferable. It is more preferable that
  • the general formula (1) -1 is preferably the following general formula (1) -1-1.
  • X 01 is a group showing a semiconductor characteristic.
  • n is an integer of 1 to 20.
  • n is an integer of 1 to 20, preferably 1 to 15, more preferably 5 to 10, and particularly preferably 7 or 10.
  • n may be any integer of 1 to 20, but is preferably 1 to 15, more preferably 5 to 10, and particularly preferably 7 or 10.
  • Step 1 First, an acetyl group is introduced into a compound exhibiting semiconductor characteristics. Next, as shown in the following reaction formula, the acetyl group is deprotected to form a hydroxyl group.
  • X 01 represents a group obtained by removing one hydrogen atom from the compound exhibiting semiconductor characteristics.
  • Step 2 Next, the compound represented by the formula (HOOC-Y ') is reacted with the compound obtained in the above step 1.
  • X 01 is a group obtained by removing one hydrogen atom from a compound exhibiting semiconductor characteristics
  • Y is a divalent linking group
  • Y ′ is a group obtained by adding one hydrogen atom to Y].
  • Step 3 Next, the compound obtained in step 2 is reacted with di (N-succinimidyl) carbonate to obtain the compound of the present embodiment.
  • X 01 is a group obtained by removing one hydrogen atom from the compound exhibiting semiconductor characteristics, and Y is a divalent linking group.
  • Examples of the solvent used in the above steps 1 to 3 include ethyl acetate, butyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, tetrahydrofuran, dioxane, N, N-dimethylformamide, N, N-dimethylacetamide, benzene, Toluene, acetonitrile, methylene chloride, chloroform, dichloroethane, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol and the like can be mentioned. These may be used alone or in combination of two or more.
  • the patterning substrate of the second embodiment of the present invention is chemically modified using the compound of the first aspect of the present invention. That is, a functional group having semiconductor characteristics is introduced onto the substrate. Therefore, the organic semiconductor material dispersed or dissolved in the semiconductor material dispersion medium in which the introduced semiconductor characteristic group and the mother skeleton are similar to each other can be suitably arranged.
  • the substrate is not particularly limited, and glass, quartz glass, silicon wafer, plastic plate, metal plate and the like are preferably mentioned. Moreover, you may use the board
  • the shape of the substrate is not particularly limited, and a flat surface, a curved surface, or a flat surface having a partially curved surface is preferable, and a flat surface is more preferable.
  • the area of the substrate is also not particularly limited, and a substrate having a surface of a size as long as the conventional coating method can be applied can be adopted.
  • pretreat the substrate surface When modifying the surface of the substrate, it is preferable to pretreat the substrate surface.
  • pretreatment with a piranha solution or pretreatment with a UV-ozone cleaner is preferable.
  • the third embodiment of the present invention is a coupling agent comprising the compound of the first embodiment.
  • the semiconductor characteristic group can be introduced to the surface of the target because it is made of a compound containing a group having semiconductor characteristics.
  • a fourth embodiment of the present invention is a pattern forming method for forming a pattern on a surface to be treated of an object, wherein at least a part of the surface to be treated of the object is aminated to form an aminated surface. It is a pattern formation method provided with the process and the 2nd process of chemically modifying the said amination surface using the compound of the 1st aspect of this invention. According to the present embodiment, it is possible to form a pattern in which a group having semiconductor characteristics is introduced on the surface of an object.
  • a substrate having an amino group is produced by causing 3-aminopropyltrimethoxysilane or the like to act on a substrate having a hydroxyl group as shown below.
  • the second step is a step of chemically modifying the aminated surface produced in the first step using the compound of the first aspect of the present invention. Since the compound of the first aspect of the present invention contains an active carbonate structure and a group having semiconductor properties, modification of the aminated substrate and introduction of a group having semiconductor properties can be simultaneously carried out.
  • the object is not particularly limited, and, for example, metals, crystalline materials (for example, single crystalline, polycrystalline and partially crystalline materials), amorphous materials, conductors, semiconductors, insulators, optical elements, painted substrates , Fiber, glass, ceramics, zeolite, plastic, thermosetting and thermoplastic materials (eg, optionally doped: polyacrylate, polycarbonate, polyurethane, polystyrene, cellulose polymer, polyolefin, polyamide, polyimide, resin, polyester, polyphenylene Etc.), films, thin films, foils, etc.
  • crystalline materials for example, single crystalline, polycrystalline and partially crystalline materials
  • amorphous materials for example, conductors, semiconductors, insulators, optical elements, painted substrates , Fiber, glass, ceramics, zeolite, plastic
  • thermosetting and thermoplastic materials eg, optionally doped: polyacrylate, polycarbonate, polyurethane, polystyrene, cellulose polymer, polyole
  • the pattern formation method of the present embodiment it is preferable to form a circuit pattern for an electronic device on a flexible substrate.
  • a foil such as a resin film or stainless steel
  • the resin film may be made of polyethylene resin, polypropylene resin, polyester resin, ethylene vinyl copolymer resin, polyvinyl chloride resin, cellulose resin, polyamide resin, polyimide resin, polycarbonate resin, polystyrene resin, vinyl acetate resin, etc. It can be used.
  • flexibility refers to the property of being able to bend the substrate without breaking or breaking even when a force of about its own weight is applied to the substrate.
  • the property of being bent by the force of its own weight is also included in the flexibility.
  • the flexibility varies depending on the material, size, thickness, environment such as temperature, etc. of the substrate. Note that although a single strip-shaped substrate may be used as the substrate, a plurality of unit substrates may be connected to form a strip.
  • the method for chemically modifying the surface to be treated of the object is not particularly limited as long as the carbonate group in the general formula (1) is a method of binding to the substrate, and known methods such as immersion method and chemical treatment method Methods can be used.
  • the chemical modification in this step can be carried out, for example, by reacting the compound having the above-mentioned general formula (1) with the substrate having an amino group produced in the previous step as shown below.
  • X 01 is a group showing a semiconductor characteristic.
  • n is an integer of 1 to 20.
  • a fifth aspect of the present invention is a method of forming a pattern on a surface to be treated of an object, wherein the treatment is carried out using a first photodegradable coupling agent containing a compound having a photoresponsive group. After the step A of aminating at least a part of the surface, and the step A, using the first coupling agent containing a compound containing a group having a semiconductor characteristic, the group having a semiconductor characteristic is treated on the surface to be treated
  • a pattern forming method comprising: introducing step B; and introducing a group having a semiconductor property using the second coupling agent containing the compound of the first aspect of the present invention after step B. It is. According to the pattern forming method 2, it is possible to introduce a group having semiconductor characteristics at high density.
  • Step A This step is a step of amination of at least a part of the surface to be treated using a first photodegradable coupling agent containing a compound having a photoresponsive group.
  • Pretreatment process Prior to the step A, it is preferable to pretreat the surface of the object before modifying the surface of the object.
  • pretreatment method pretreatment with a piranha solution or pretreatment with a UV-ozone cleaner is preferable.
  • the object the same one as the subject described in the patterning method of the fourth aspect of the present invention can be used.
  • the amination in step A is not particularly limited as long as the first photodegradable coupling agent containing a compound having a photoresponsive group is a method of binding to a substrate, and known methods such as immersion method and chemical treatment method Methods can be used.
  • the compound having a photoresponsive group contained in the photodegradable silane coupling agent used in step A is not particularly limited as long as it is a material capable of modifying the surface to be treated to be water repellent.
  • step A after the first photodegradable coupling agent is bound to the substrate, the degradable group is dissociated in the exposed area by exposing the surface to be treated with light of a predetermined pattern, and the amino acid having hydrophilic performance A group is formed.
  • the light irradiated at the time of exposure is preferably ultraviolet light.
  • the light to be irradiated preferably includes light having a wavelength within the range of 200 nm to 450 nm, and more preferably includes light having a wavelength within the range of 320 nm to 450 nm. It is also preferable to emit light including light with a wavelength of 365 nm.
  • the light having these wavelengths can efficiently decompose the photolytic group.
  • As a light source low pressure mercury lamp, high pressure mercury lamp, super high pressure mercury lamp, xenon lamp, sodium lamp; gas laser such as nitrogen, liquid laser of organic dye solution, solid laser containing rare earth ion in inorganic single crystal, etc. It can be mentioned.
  • a light source other than a laser capable of obtaining monochromatic light light of a specific wavelength obtained by extracting a wide-band line spectrum or a continuous spectrum using an optical filter such as a band pass filter or a cutoff filter may be used.
  • a high pressure mercury lamp or an ultrahigh pressure mercury lamp is preferable as a light source because a large area can be irradiated at one time.
  • light can be emitted arbitrarily within the above range, but it is particularly preferable to emit light energy of distribution corresponding to the circuit pattern.
  • the photolytic group is dissociated to generate an amino group.
  • the pattern is preferably a circuit pattern, and it is preferable to form the circuit pattern on a flexible substrate.
  • Step B This step is a step of introducing a group having semiconductor characteristics on the surface to be treated using the first coupling agent containing a compound containing a group having semiconductor characteristics after the step A.
  • step B for example, compound B described later can react with the unmodified hydroxyl group remaining in step A to introduce a group having semiconductor properties on the surface of the object. It is preferable to use the compound B mentioned later as a compound containing the group which has a semiconductor characteristic which a 1st coupling agent contains.
  • Step C This step is a step of introducing a group having semiconductor characteristics using the second coupling agent containing the compound of the first aspect of the present invention after the step B.
  • the description of the step C is the same as the description of the second step of the pattern formation method of the fourth aspect of the present invention.
  • the first coupling agent containing a group having a semiconductor property and the second coupling can be modified in multiple steps to introduce a group having a semiconductor property on the substrate surface.
  • Step D is a step of arranging a pattern forming material on the formed pattern.
  • the semiconductor characteristic group be introduced at a high density.
  • transducing a semiconductor characteristic group is reduced. According to this embodiment, since the group having semiconductor characteristics is introduced in multiple stages, semiconductor characteristic groups can be introduced at high density.
  • the second coupling agent used in step C uses the compound of the first aspect of the present invention.
  • the compound of the first aspect can reduce the surface roughness after the introduction of the semiconductor characteristic group by adjusting the length of the alkylene chain which is the linker structure. Specifically, if it demonstrates using said example, the unevenness
  • strand so that it may become "n1 3 + n", and surface roughness can be reduced.
  • the pattern forming method of the fourth aspect of the present invention and the pattern forming method of the fifth aspect preferably further include a step D. That is, in the pattern formation method of the fourth aspect, the pattern formation method of the fifth aspect preferably comprises the first step, the second step and the step D in this order, the step A, the step B, the step Preferably, C and step D are provided in this order.
  • Step D This step is a step of arranging a pattern forming material in the area where the pattern is formed.
  • a conductive material in which particles of gold, silver, copper or alloys thereof are dispersed in a predetermined solvent, or a precursor solution containing the above-mentioned metal, an insulator (resin),
  • a precursor solution containing the above-mentioned metal, an insulator (resin) examples thereof include electronic materials in which a semiconductor, an organic EL light emitting material and the like are dispersed in a predetermined solvent, and a resist solution. Above all, it is preferable to dispose an electronic material as a pattern forming material.
  • the pattern formation material is preferably a conductive material, a semiconductor material, or an insulating material, and among them, the semiconductor material can be suitably disposed.
  • the conductive material examples include a pattern forming material made of a dispersion liquid in which conductive fine particles are dispersed in a dispersion medium.
  • conductive fine particles for example, metal fine particles containing any of gold, silver, copper, palladium, nickel and ITO, these oxides, and fine particles of conductive polymer and superconductor, etc. are used.
  • These conductive fine particles can also be used by coating an organic substance or the like on the surface in order to improve the dispersibility.
  • the dispersion medium is not particularly limited as long as it can disperse the above-mentioned conductive fine particles and does not cause aggregation.
  • alcohols such as methanol, ethanol, propanol and butanol, n-heptane, n-octane, decane, dodecane, tetradecane, tetradecane, toluene, xylene, cymene, durene, indene, dipentene, tetrahydronaphthalene, decahydro Hydrocarbon compounds such as naphthalene and cyclohexylbenzene, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol methyl ethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, 1,2-dimethoxyethane, bis (2-
  • water, alcohols, hydrocarbon compounds, and ether compounds are preferable in terms of the dispersibility of the fine particles, the stability of the dispersion, and the ease of application to the droplet discharge method (ink jet method),
  • water and a hydrocarbon type compound can be mentioned.
  • an organic semiconductor material composed of a dispersion liquid dispersed or dissolved in a dispersion medium can be used.
  • a low molecular weight material or a high molecular weight material of ⁇ electron conjugated system whose skeleton is composed of conjugated double bonds is desirable.
  • soluble low molecular weight materials such as acenes such as pentacene, and thienoacenes such as benzothienobenzothiophene
  • soluble high molecular weight materials such as polythiophene, poly (3-alkylthiophene) and polythiophene derivatives can be mentioned.
  • a soluble precursor material may be used which is converted to the above-described semiconductor by heat treatment, and examples of the pentacene precursor include sulfinylacetamide pentacene and the like.
  • the present invention is not limited to the organic semiconductor material, and an inorganic semiconductor material may be used.
  • Insulating materials are represented by polyimide, polyamide, polyester, acrylic, PSG (phosphor glass), BPSG (phosphoboron glass), polysilazane SOG, silicate SOG (Spin on Glass), alkoxysilicate SOG, and siloxane polymer.
  • An insulating material comprising a dispersion in which SiO 2 or the like having a Si—CH 3 bond is dispersed or dissolved in a dispersion medium can be mentioned.
  • positioned in the process D use the pattern formation material in which the group which has the semiconductor characteristic introduce
  • a droplet discharge method As a method of arranging a pattern forming material, a droplet discharge method, an inkjet method, a spin coat method, a roll coat method, a slot coat method, a dip coat method, or the like can be applied.
  • the compound A is a compound represented by the following general formula (A).
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R 01 and R 02 Each independently represents a hydrocarbon group which may have a substituent
  • n represents an integer of 0 or more.
  • X is a halogen atom or an alkoxy group.
  • the halogen atom represented by X can include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, but X is preferably an alkoxy group rather than a halogen atom.
  • n represents an integer, and is preferably an integer of 1 to 20, and more preferably an integer of 2 to 15 from the viewpoint of the availability of starting materials.
  • R 1 is a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms.
  • a linear or branched alkyl group having 1 to 5 carbon atoms is preferable, and specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group Groups, tert-butyl group, pentyl group, isopentyl group, neopentyl group and the like.
  • cyclic alkyl groups include groups in which one or more hydrogen atoms have been removed from a polycycloalkane such as a monocycloalkane, bicycloalkane, tricycloalkane or tetracycloalkane.
  • R 1 is preferably a hydrogen atom, a methyl group, an ethyl group or an isopropyl group, and more preferably a methyl group or an isopropyl group.
  • R 01 and R 02 each independently represent a hydrocarbon group which may have a substituent.
  • a hydrogen atom (—H) may be substituted with a monovalent group, and a methylene group (—CH 2 —) may be divalent. Both cases of substitution with a group are included.
  • a hydrocarbon group of R 01 and R 02 a linear or branched alkyl group can be mentioned.
  • the linear alkyl group preferably has 1 to 20 carbon atoms.
  • Compound 1 can be made to be a water repellent compound if the alkyl group as a hydrocarbon group of R 01 and R 02 is a long chain alkyl group having 10 or more carbon atoms.
  • R 01 and R 02 may have in the general formula (A), a substituent containing an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxyl group, a carbonyl group and a hetero atom Etc.
  • the alkyl group as the substituent is preferably an alkyl group having a carbon number of 1 to 5, and most preferably a methyl group, an ethyl group, a propyl group, an n-butyl group or a tert-butyl group.
  • the alkoxy group as the substituent is preferably an alkoxy group having a carbon number of 1 to 5, and is preferably methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy or tert-butoxy, methoxy And ethoxy groups are most preferred.
  • a halogen atom as the said substituent a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned, A fluorine atom is preferable.
  • a halogenated alkyl group as said substituent the group by which one part or all part of the hydrogen atom of the said alkyl group was substituted by the said halogen atom is mentioned.
  • n is an integer of 0 or more. In the present embodiment, n is preferably 3 or more. Further, n is preferably 10 or less, more preferably 5 or less. The upper limit value and the lower limit value can be arbitrarily combined.
  • the compound (A) represented by the general formula (A) is preferably a fluorine-containing compound (A) -1 represented by the following general formula (A) -1.
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R f1 , R f2 is each independently a fluorinated alkoxy group
  • n represents an integer of 0 or more.
  • R f1 and R f2 are each independently a fluorinated alkoxy group.
  • the fluorinated alkoxy group of R f1 and R f2 is preferably an alkoxy group having a carbon number of 3 or more, and may be partially fluorinated; It may be a fluoroalkoxy group. In the present embodiment, a partially fluorinated fluorinated alkoxy group is preferred.
  • the n f1 is an integer of 0 or more
  • n f2 is an integer of 0 or more.
  • the fluorinated alkoxy groups of R f1 and R f2 may be the same or different, but are preferably the same from the viewpoint of easiness of synthesis.
  • the fluorinated alkoxy group of R f1 and R f2 is preferably a long chain fluoroalkyl chain.
  • n f1 is preferably 0 to 10, more preferably 0 to 5, particularly preferably 0 to 3, and most preferably 3.
  • n f2 is preferably 1 to 15, more preferably 4 to 15, particularly preferably 6 to 12, and most preferably 7 to 10.
  • the compound A1 is a compound represented by the following general formula (A1).
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R 01 and R 02 Each independently represents a hydrocarbon group which may have a substituent
  • n represents an integer of 0 or more.
  • the compound (A1) represented by the general formula (A1) is preferably a fluorine-containing compound (A1) -1 represented by the following general formula (A1) -1.
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R f1 , R f2 is each independently a fluorinated alkoxy group
  • n represents an integer of 0 or more.
  • Compound B is a compound represented by the following general formula (B).
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R 12 represents a thiophene skeleton Is a substituent having n represents an integer of 0 or more.
  • R 1 n description of R 1, n is the same as the description of X, for R 1, n in the general formula (A).
  • substituent having a thiophene skeleton of R 12 include groups represented by any of the following (R 12 -1) to (R 12 -3).
  • the compound B may be a compound (B1) represented by the following general formula (B1).
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R 12 represents a thiophene skeleton Is a substituent having L is a divalent linking group containing (-NH-) and a methylene group.
  • the compound (B1) can be obtained by reacting the silane compound with the compound represented by the general formula (1) to change the active carbonate structure.
  • the compound represented by the general formula (1) can simultaneously carry out the modification of the aminated substrate and the introduction of the semiconductor characteristic group.
  • a material having a semiconductor property can be introduced to the surface of the object having a hydroxyl group.
  • the compound (B1) is preferably a compound (B1) -1 represented by the following general formula (B1) -1.
  • X represents a halogen atom or an alkoxy group
  • R 1 represents a hydrogen atom or a linear, branched or cyclic alkyl group having 1 to 10 carbon atoms
  • R 12 represents It is a substituent having a thiophene skeleton.
  • n represents an integer of 0 or more.
  • R 1, n is the same as the description of X, for R 1, n in the general formula (A).
  • substituent having a thiophene skeleton of R 12 include groups represented by any of the above (R 12 -1) to (R 12 -3).
  • n can be any integer of 1 to 20, preferably 1 to 15, more preferably 5 to 10, and particularly preferably 7 or 10.
  • a substrate processing apparatus 100 which is a roll-to-roll apparatus as shown in FIG. It may be used to form a pattern.
  • the structure of the substrate processing apparatus 100 is shown in FIG.
  • the substrate processing apparatus 100 performs processing on a substrate supply unit 2 that supplies a strip-shaped substrate (for example, a strip-shaped film member) S, and a surface (processed surface) Sa of the substrate S.
  • the substrate processing unit 3, the substrate recovery unit 4 for recovering the substrate S, the application unit 6 of the compound of the first embodiment, the exposure unit 7, the mask 8, the pattern material application unit 9, and these units And a controller CONT to control.
  • the substrate processing unit 3 can execute various processes on the surface of the substrate S after the substrate S is sent out from the substrate supply unit 2 and before the substrate recovery unit 4 recovers the substrate S.
  • This substrate processing apparatus 100 can be suitably used, when forming display elements (electronic device), such as an organic EL element and a liquid crystal display element, on a substrate S, for example.
  • FIG. 1 illustrates a method of using a photomask to generate desired pattern light
  • the present embodiment may be suitably applied to a maskless exposure method that does not use a photomask. it can.
  • a maskless exposure method of generating pattern light without using a photomask a method of using a spatial light modulation element such as DMD, a method of scanning a spot light as in a laser beam printer, and the like can be mentioned.
  • an XYZ coordinate system is set as shown in FIG. 1, and the following description will be made using this XYZ coordinate system as appropriate.
  • the XYZ coordinate system for example, an X axis and a Y axis are set along a horizontal surface, and a Z axis is set upward along the vertical direction.
  • the substrate processing apparatus 100 transports the substrate S along the X axis as a whole from the minus side ( ⁇ side) to the plus side (+ side). At that time, the width direction (short direction) of the strip-like substrate S is set in the Y-axis direction.
  • the resin film may be made of polyethylene resin, polypropylene resin, polyester resin, ethylene vinyl copolymer resin, polyvinyl chloride resin, cellulose resin, polyamide resin, polyimide resin, polycarbonate resin, polystyrene resin, vinyl acetate resin, etc. It can be used.
  • the substrate S preferably has a small thermal expansion coefficient so that the dimensions do not change even if it receives heat of, for example, about 200.degree.
  • an inorganic filler can be mixed with a resin film to reduce the thermal expansion coefficient.
  • the inorganic filler include titanium oxide, zinc oxide, alumina, silicon oxide and the like.
  • the substrate S may be a single layer of ultrathin glass having a thickness of about 100 ⁇ m manufactured by the float method or the like, or a laminate in which the above-mentioned resin film or aluminum foil is bonded to the ultrathin glass.
  • the dimension in the width direction (short direction) of the substrate S is, for example, about 1 m to 2 m, and the dimension in the longitudinal direction (long direction) is, for example, 10 m or more.
  • this dimension is only an example, and is not limited to this.
  • the dimension in the Y direction of the substrate S may be 50 cm or less, or 2 m or more.
  • the dimension of the substrate S in the X direction may be 10 m or less.
  • the substrate S is preferably formed to have flexibility.
  • flexibility refers to the property of being able to bend the substrate without breaking or breaking even when a force of about its own weight is applied to the substrate.
  • the property of being bent by the force of its own weight is also included in the flexibility.
  • the flexibility varies depending on the material, size, thickness, environment such as temperature, etc. of the substrate. Note that although a single strip-shaped substrate may be used as the substrate S, a plurality of unit substrates may be connected to form a strip.
  • the substrate supply unit 2 feeds and supplies, for example, the substrate S wound in a roll shape to the substrate processing unit 3.
  • the substrate supply unit 2 is provided with a shaft portion around which the substrate S is wound, a rotation driving device which rotates the shaft portion, and the like.
  • a cover provided to cover the substrate S in a rolled state may be provided.
  • the substrate supply unit 2 is not limited to a mechanism for delivering the substrate S wound in a roll, but includes a mechanism (for example, a nip type drive roller) for sequentially delivering the strip-like substrate S in its length direction. I hope there is.
  • the substrate recovery unit 4 rolls up and recovers the substrate S which has passed through the substrate processing apparatus 100, for example, in a roll shape. Similar to the substrate supply unit 2, the substrate recovery unit 4 is provided with a shaft for winding the substrate S, a rotational drive source for rotating the shaft, and a cover for covering the collected substrate S. When the substrate S is cut into a panel shape in the substrate processing unit 3, the substrate S is collected in a state different from the state of being wound in a roll shape, for example, the substrate S is collected in a stacked state. It does not matter.
  • the substrate processing unit 3 transports the substrate S supplied from the substrate supply unit 2 to the substrate recovery unit 4 and uses the compound of the first embodiment for the processing surface Sa of the substrate S in the process of transport.
  • a step of chemically modifying, a step of irradiating light of a predetermined pattern onto the chemically modified treated surface, and a step of arranging a patterning material are performed.
  • the substrate processing unit 3 applies a compound application unit 6 that applies the compound of the first embodiment to the surface to be processed Sa of the substrate S, an exposure unit 7 that emits light, a mask 8, and a pattern material application unit 9.
  • a transport device 20 including a drive roller R for feeding the substrate S under conditions corresponding to the form of processing.
  • the compound application unit 6 and the pattern material application unit 9 are droplet application devices (for example, droplet discharge type application devices, inkjet type application devices, spin coat type application devices, roll coat type application devices, slot coat type application devices, etc. Can be mentioned.
  • Each of these devices is appropriately provided along the transport path of the substrate S, and a flexible display panel or the like can be produced by a so-called roll-to-roll method.
  • the exposure unit 7 is provided, and an apparatus that takes charge of steps before and after that (photosensitive layer forming step, photosensitive layer developing step, etc.) is also provided inline as necessary.
  • reaction solution was then poured into 100 mL of water and 100 mL of dichloromethane was added.
  • the aqueous layer and the organic layer were separated, and the organic layer was washed with water (50 mL ⁇ 6) and brine (100 mL).
  • the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. It was isolated and purified by recrystallization (toluene 300 mL, 70 ° C.) and dried under vacuum to obtain a pale yellow solid.
  • reaction solution was concentrated, dissolved in 60 mL of chloroform, 20 mL of water and 5 mL of 2N hydrochloric acid were added, and the mixture was separated into an aqueous layer and an organic layer.
  • the mixture was further extracted with chloroform (20 mL ⁇ 2), and the organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and vacuum dried to obtain a white solid.
  • BBT is a group represented by the above (R 12 -1).
  • Substrate CONT Control unit Sa: Surface to be treated 2 ... Substrate supply unit 3 ... Substrate treatment unit 4 ... Substrate recovery unit 6 ... Compound application unit 7 .. Exposure unit 8: Mask 9: Pattern material application unit 100: Substrate processing device

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  • Spectroscopy & Molecular Physics (AREA)
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  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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Abstract

L'invention concerne un composé, un substrat de formation de motif, un agent de couplage et un procédé de formation de motif. Le composé est représenté par la formule générale (1). [Dans la formule, X01 est un groupe représentant des caractéristiques de semi-conducteur, et Y est un groupe de liaison divalent.]
PCT/JP2018/026909 2017-07-19 2018-07-18 Composé, substrat de formation de motif, agent de couplage et procédé de formation de motif WO2019017386A1 (fr)

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TWI753188B (zh) 2022-01-21
JP6917815B2 (ja) 2021-08-11
TW201908290A (zh) 2019-03-01

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